Best apartment offers in Chicago, IL

13595 available apartment offers

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Chicago, IL apartments
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13595 Holiday apartments in Chicago, IL

Best family friendly Chicago, IL Holiday Apartments and Self Contained Accommodations

Among the 13595 accommodations in Chicago, IL, here are the 4 best family friendly holiday apartments

1f Cozy Home In Little Italy Near Downtown West Loop United Center - Chicago, IL
9.5 102 reviews

1f Cozy Home In Little Italy Near Downtown West Loop United Center

apartment, Chicago
This Chicago apartment rental is situated in Little Italy, approximately 1.8km from the United Centre and under 5km from downtown attractions such as the Art Institute of Chicago and the Willis Tower.
The 93 square metre property offers three bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, in-unit laundry, private parking, and free Wi-Fi.
The Grand Kimball Lodge, Logan Square, Sleeps 21 - Chicago, IL
9.9 65 reviews

The Grand Kimball Lodge, Logan Square, Sleeps 21

apartment, Chicago
This Logan Square apartment in Chicago offers spacious 5-bedroom accommodation, sleeping up to 16 guests, and is conveniently located for exploring the city's attractions; precise distances to landmarks would depend on the exact address within Logan Square.
The property boasts two fully equipped kitchens, two living areas, a unique glamping tent, and access to a further bedroom, bathroom, and kitchen/dining area, all within a Wes Anderson-inspired design.
Classic Posh Home Chicago Roscoe Village+ Wrigley - Chicago, IL
9.9 106 reviews

Classic Posh Home Chicago Roscoe Village+ Wrigley

apartment, Chicago
This upscale Victorian-style flat is situated in a prime Chicago location, one block from excellent restaurants and shops, and within easy walking distance (approximately 0.8 kilometres) of Wrigley Field.
The one-bedroom, one-bathroom apartment sleeps two guests and boasts a chef's kitchen, marble steam bath, stained-glass windows, Bose music system, Smart TV, high-speed internet, and a well-stocked pantry; parking is also available.
Beautiful 2br Apartment In Old Town - Chicago, IL
9.8 298 reviews

Beautiful 2br Apartment In Old Town

apartment, Chicago
This Old Town apartment is situated in Chicago's Old Town Historic District, blocks from Lincoln Park and North Avenue Beach, offering easy access to the Red and Brown Line 'L' train stations.
The two-bedroom, one-bathroom flat sleeps six, features a modern kitchen with stainless steel appliances, and includes amenities such as air conditioning, a fitness centre, parking and August smart lock for contactless check-in.

Best Chicago, IL holiday apartments with a balcony

Elegant 2br With Resort Amenities & City Views - Chicago, IL
10 5 reviews

Elegant 2br With Resort Amenities & City Views

apartment, Chicago
This Magnificent Mile flat, near Washington Square Park and the Museum of Contemporary Art in downtown Chicago, offers easy access to Michigan Avenue's shops and iconic landmarks such as the Water Tower.
The 110 square metre dwelling boasts two bedrooms with queen-size beds, two bathrooms, and sleeps up to seven guests, featuring a high-end kitchen, private balcony, and access to a building with a pool, hot tub, fitness centre, and rooftop sky club.
Mich Ave Downtown 2bd, Grant Park Museums 25 - Chicago, IL
9.7 843 reviews

Mich Ave Downtown 2bd, Grant Park Museums 25

apartment, Chicago
This Chicago apartment is located in the Grant Park district, a short walk from the Museum Campus, Soldier Field, and Grant Park, making it ideal for exploring the city's cultural attractions. The apartment has received excellent ratings for location, cleanliness, and user experience.
The apartment is a spacious two-bedroom flat with two bathrooms, comfortably accommodating up to six guests. The apartment has a fully equipped kitchen, a balcony, a garden, and parking, offering a comfortable and convenient stay.
Feelin Nauti Near Wrigley - Chicago, IL
No reviews

Feelin Nauti Near Wrigley

apartment, Chicago
This one-bedroom flat is situated in Chicago's Lakeview district, within a 10-minute walk of Wrigley Field, Southport Corridor shops, and Boystown nightlife, with the Addison Brown Line 'L' train station just 550 metres away.
Guests can enjoy exclusive use of the entire first floor of a duplex, accommodating two people with one bathroom, air conditioning, a kitchen equipped with a fridge, microwave, and dishwasher, and a complimentary parking space, plus a free membership to The Metropolitan for stays under 14 days.
New! Spacious Art Deco Modern 5 Bd/3ba Condo - Chicago, IL
8.5 2 reviews

New! Spacious Art Deco Modern 5 Bd/3ba Condo

apartment, Chicago
This spacious Chicago apartment, located near the United Center, Water Tower Place, and Union Station (all within a 3-5 km radius), offers easy access to major attractions.
The 279 square metre property boasts a five-bedroom, three-bathroom layout sleeping up to 27 guests, complete with a fully equipped kitchen, free Wi-Fi, private parking, and a terrace.

Frequently asked questions about apartment rentals in Chicago, IL

  • What are the must-see attractions for a 2 days stay in Chicago, IL?

    For a two-day trip, you can't miss the iconic Willis Tower (formerly Sears Tower) for panoramic views of the city. Then, explore Millennium Park, home to Cloud Gate, nicknamed 'The Bean', and the Crown Fountain with its interactive water displays. Finally, stroll along Navy Pier for its Ferris wheel, shops, and restaurants.
  • What are the best apartments in Chicago, IL?

  • Which neighborhoods in Chicago, IL are best for renting an apartment?

    For a vibrant, walkable neighbourhood, consider Lincoln Park with its green spaces and Lake Michigan access. If you prefer a more historic feel, try the Gold Coast, known for its elegant architecture. For a more affordable option with great restaurants and nightlife, check out Wicker Park.
  • What are the best apartments with a pool in Chicago, IL?

  • What are the top cultural and historical sites in Chicago, IL?

    Chicago is brimming with cultural and historical gems. The Art Institute of Chicago houses masterpieces by Monet and Van Gogh, while the Field Museum boasts dinosaur skeletons and ancient Egyptian artefacts. For a taste of history, visit the Chicago Cultural Center, a stunning building with free concerts and exhibitions, or the Museum of Science and Industry.
  • What are the best apartments with a jacuzzi in Chicago, IL?

  • What makes Chicago, IL unique or famous?

    Chicago is known for its stunning architecture, from the towering skyscrapers of the Loop to the charming brownstones of the Gold Coast. It's also a culinary powerhouse, with world-class restaurants and a renowned deep-dish pizza scene. And don't forget the vibrant arts and culture scene, with world-class museums, theatres, and music venues.
  • What are the best apartments for families and kids in Chicago, IL?

  • Where can you find the best local markets and street food in Chicago, IL?

    For a taste of Chicago's diverse food scene, head to Maxwell Street Market on Sundays for a mix of local produce, crafts, and street food. The Wicker Park Farmers Market on Saturdays offers fresh, seasonal produce, while the Green City Market in Lincoln Park has a wide selection of local vendors.
  • What are the best pet friendly apartments in Chicago, IL?

  • How is the public transportation system in Chicago, IL?

    Chicago has a reliable and extensive public transportation system, the 'L', which is a combination of elevated trains and underground subway lines. It's a great way to get around the city, especially during rush hour. You can also use the CTA buses for more local travel.
  • What are the best apartments with parking in Chicago, IL?

  • Which seasonal events or festivals should apartment renters look forward to in Chicago, IL?

    Chicago is a city that comes alive with seasonal events. In the spring, enjoy the Chicago Blues Festival, while summer brings the Taste of Chicago food festival. Autumn is perfect for the Chicago Marathon, and winter offers festive holiday markets and ice skating at Millennium Park.
  • What amenities are typically included in apartments in Chicago, IL?

    Apartments in Chicago typically include central heating and air conditioning, in-building laundry facilities, and sometimes a gym or a rooftop terrace. Some newer buildings may also offer amenities like a swimming pool, a dog park, or a resident lounge.
  • What leisure activities are available for relaxation in Chicago, IL?

    For relaxation, Chicago offers a variety of options. You can stroll along the Lakefront Trail for stunning views of Lake Michigan, visit the Lincoln Park Zoo for a free day out, or take a boat tour on the Chicago River. For a quieter experience, explore the Garfield Park Conservatory, a beautiful greenhouse with exotic plants.

Popular destinations

Best Chicago, IL holiday apartments with parking

Fully Updated Jr. 1 Bed, Steps From Lincoln Park - Chicago, IL
9.8 20 reviews

Fully Updated Jr. 1 Bed, Steps From Lincoln Park

apartment, Chicago
This stylish one-bedroom flat in Chicago's Lincoln Park district offers immediate access to Lincoln Park, the lakefront, and is just a short walk to shops, restaurants, and public transport.
This well-appointed condo comfortably accommodates up to four guests with a queen-size bed and a queen sofa bed, featuring a fully equipped kitchen, air conditioning, and Wi-Fi for a convenient stay.
Guest Nest Oak Park 321_3 - Chicago, IL
9.7 27 reviews

Guest Nest Oak Park 321_3

apartment, Oak Park
This Oak Park studio apartment is situated in the near-west suburbs, a convenient 0.8km walk from Oak Park's town centre, offering easy access to shops and restaurants.
The ground-floor, pet-friendly self-catering unit sleeps three, features a fully equipped kitchen including a dishwasher, private patio, and high-speed internet; extended-stay discounts are available.
Penthouse With Private Rooftop And Skyline Views - Sleeps 6 - Chicago, IL
9.3 3 reviews

Penthouse With Private Rooftop And Skyline Views - Sleeps 6

apartment, Chicago
This two-bedroom flat is situated approximately 2.8 kilometres from the United Centre, 3.1 kilometres from the Chicago Water Tower, and 3.2 kilometres from Union Station, offering city views from its private rooftop.
This 60 square metre residence includes two bathrooms, a fully equipped kitchen with a fridge and microwave, air conditioning, complimentary Wi-Fi, and a patio, accommodating up to eleven guests with a check-out time of 11:00.
2r- ️ Stylish And Cozy 2br In Logan Square! - Chicago, IL
9.9 273 reviews

2r- ️ Stylish And Cozy 2br In Logan Square!

apartment, Chicago
This Chicago apartment, conveniently located near a dog park and offering easy street parking, provides a self-check-in experience.
The 79 square metre (850 square foot) two-bedroom flat sleeps four, features a fully equipped kitchen with granite worktops, modern appliances and fast Wi-Fi, plus a garden.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

Trendy Chicago Apartment - Free Parking Spot - Chicago, IL
9.7 286 reviews

Trendy Chicago Apartment - Free Parking Spot

apartment, Chicago
This Logan Square flat is conveniently located near a Divvy bike station and the Bloomingdale Trail (the 606), offering easy access to Chicago's attractions.
The two-bedroom apartment, sleeping four, boasts a well-equipped kitchen with retro fridge, high-speed internet, keyless entry, on-site laundry, and free parking; nearby activities include exploring the 606 Trail or cycling around the neighbourhood.
Garage Parking! Walk To Logan Square Station Plus Great Local Restaurants And Bars - Chicago, IL
9.5 332 reviews

Garage Parking! Walk To Logan Square Station Plus Great Local Restaurants And Bars

apartment, Chicago
This three-bedroom duplex apartment is situated in Chicago's Logan Square, a short walk from the Logan Square Blue Line station, offering easy access to Chicago's attractions.
The property boasts a duplex layout, sleeping up to seven guests, and includes amenities such as a fully equipped kitchen with dishwasher, garage parking, and essential toiletries; nearby restaurants and bars provide ample entertainment options.
Cozy 3 Bedroom  5min To Downtown-mccormick Place - Chicago, IL
9.7 6 reviews

Cozy 3 Bedroom 5min To Downtown-mccormick Place

apartment, Chicago
This three-bedroom Chicago apartment, sleeping up to six guests comfortably plus one on a sofa bed, is situated in a peaceful neighbourhood, a 0.8-kilometre walk from Chinatown and its diverse restaurants and shops.
The 3-bedroom flat offers a newly renovated kitchen with stainless steel appliances, a garden, free on-street parking, and air conditioning, ideal for families or groups exploring the city.
Stylish Pilsen Retreat | 10 Minutes From Downtown - Chicago, IL
9.3 42 reviews

Stylish Pilsen Retreat | 10 Minutes From Downtown

apartment, Chicago
This Pilsen flat is situated approximately 6.4 kilometres from Chicago's city centre, offering easy access to major attractions.
The one-bedroom apartment sleeps four guests, featuring a fully equipped kitchen with dishwasher, two Smart TVs, in-building laundry, and a spa-like bathroom; high-speed Wi-Fi and pet-friendliness are also included.
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